My Boss, Myself and I

By Beckie2309

Original link:

Tags: boss, coworker, cupid, accidental, unprotected, oral, sex

Added: 26 Apr 2013 Views: 12044 Avg Score: 4.63

In an attempt to set up my boss with a co-worker, his affection turns elsewhere.
Sitting on my desk, swaying my legs, I was conjuring another one of my ‘cupid attacks’ on two colleagues. I was quite good at it, having set up four couples and one of them getting engaged within the year. It was something that thrilled me but also depressed me as I was cupid for everyone else, but if only cupid would shoot an arrow in my ass…

Woe is me.

My own lack of a love life wasn't due to being unattractive. Not to be vain but I'm quite good looking. I have dark brown hair that waves naturally, piercing blue eyes and a thin and curvy figure to finish. I guess men didn't like brunettes as I much as I thought they did. Or blue eyes. Anyway, I got my kicks from setting up others, and that was my plan!

Scanning the cubicles from my office, I sighed. There was no-one compatible in my eyes.

That’s when my boss popped into mind; at the same time my assistant walked into my office. Light bulbs flashed above my head and I knew who my next candidates were. 

Sam and Alicia.

“Miss Wickes, could I have your reports please? Mr. Clark needs them,” spoke Alicia with her nervousness in tow.

“Sure, Lis. Here.”

She smiled at my pet name for her; I had taken her under my wing when she started and she had told me about her mini crush on my boss. 

She's the perfect candidate.

“In fact, I’ll take them to him. I need to have a quick word.” I jumped down from my desk in my nude, stocking clad feet, pulling down my navy blue pencil skirt as I sashéd through my office door and the cubicles to his office.

I raised my hand to knock at the door. It opened as my hand followed, smacking my boss in the face. 

Well that wasn't meant to happen.

“Shit, Sam. I am so sorry!”

I fussed over him but he dismissed my efforts in checking his face ‘claiming’ he was fine.

“It’s a good job I like you, Nicole,” he said wiping a stay tear from the corner of his eye. 

Ever so formal with the full name, jeeeez.

“Can I come in? I need to discuss something with you,” I asked, already making my way into his office.

I was glad of our formal/informal friendship.

“Sure, I guess I have no choice,” he said sarcastically. 

What a tool.

“If I ask you a question, will you give me an honest answer?” I blurted after turning abruptly, being much closer to Sam than I intended.

“Go ahead,” he answered, sighing.

“What are your opinions on Alicia Burkard?” I asked with a gleam in my eye.

“Oh no you don’t, I'm not falling for cupid's trap. You can piss off if you thing you’re hooking me up with some stranger,” he defended.

“Ooohh, I can sense some denial in there! You like her! It’s difficult to pull the wool over my eyes and I can read you like a book!” I smiled, claiming victory.

“You’d be wrong there Nic,” he whispered.

“And why is that?” I asked, looking up to his face rather than meeting it as I was lacking my stilettos. 

Plus, a new name for me, hmm?

He raised his eyes to mine and they were filled with what, Love? Lust? Confusion? For me!? It was like he was pleading for me to realise.

The colour drained from my face and I stood dumbstruck. 

Fuck me I'm so blind.

“Shit,” I whispered. I backed away from him and left his office.

How could I be so open with him now? Now, he's basically dropped a massive bombshell like that. My mother said to never meddle, never! And this happened; my sodding boss wanted me!

I walked through my office and fell against the dark oak door after I shut it, sliding down until I sat on the floor with my knees to my chest. I always had weak spot for Sam but I never thought the feelings would be mutual.

I was the one who shot cupid's arrow, not received it. I was lost in my thought and almost didn't notice my door pulsing to open. I stood, placing my shoes back on and welcomed in two associates of the company. At least this would take my mind of the recent revelation. Hopefully.

Julia, Mark and I spend almost three hours discussing business plans and I was almost falling off my chair by the time it was finished. Working through dinner wasn't normal for me and I had missed all the appointments I had for the day due to the meeting overrunning.

I sat in my office alone on the love seat across from my desk. Being alone was total bliss. I brought my legs up, closed my eyes, and then sleep over took me.


I awoke a few hours later, rubbing my eyes and checking my watch. Shit, it was 9:30pm. I wondered what had woken me as I usually sleep anywhere. That was when I noticed the gentle tapping on my office door. I sat upright and stretched, rubbing my eyes while feeling my chest tighten against my silk blouse, not the most comfortable item of clothing I owned but flattering.

I opened my door with a nonchalant expression. When it was open to its full capacity, I made sleepy eye contact with Sam and shut the door again with a gentle slam, acting as if no-one was on the other side.

Ignoring a man that is in to you? Daft women! My mind was speaking sense but I shook my head, as I was too tired to care about anything. As I heard footsteps going away from my office, I pulled on my heels and coat before turning off my desk lamp and leaving my office to go home.


I was glad to be home. The sofa looked so tempting, I made it no further and simply collapsed fully clothed.

I awoke at about 3am, bolting upright on my sofa. I was surprisingly alert and focused, but not focused enough to notice my door nearly being knocked off its hinges.

“What the hell?” I whispered under my breath as I walked to my door. Not knowing my shirt had come undone during my sleep, I flung my door open in half rage and half curiosity.


“What the hell are you doing here? How do you even know where I live?” I asked, confused.

“It’s on work files.”

I have to admit, I asked a pretty daft question.

“Answer my first question Sam,” I asked.

“I'm confused Nic. You’re such an attractive women, with a heart of gold, and you play cupid, making everyone else happy and forgetting about your fucking self, not noticing what is in front of your god damned eyes!” he started to raise his voice in frustration.

“And what is that?” I wasn't being sarcastic; I was oblivious to these things.

“That ever since that damn ass of yours was swaying down the corridor to my office, and you walked with such confidence and spoke with it too, I was smitten by you? That was four fucking years ago when you were sixteen and I can’t bite my tongue any more. Nic, the only person I have opinions about in the office is you!” he was shouting at this point and I was shocked, to say the least.

“Well, that was… enlightening.” I had nothing else to say. I wasn't going to fall to my knees and confess my love to him there and then.

“Screw this,” he said before leaping into my house and pulling me to his lips.

The kiss was so soft and gentle, it was as if he expected me to push away, but how could I? I melted against his lean body and returned his kiss with force.

“Your shirt’s undone,” he whispered after the kiss.

“It just makes your job easier,” I retorted.

He pushed me again the wall hoisted me up so my weight rested on his hips. I was taken by surprise and was soon receiving another kiss, fuelled by lust and need.

He placed his hands on my ass and hoisted me over his shoulder, into the fireman’s lift, carrying me upstairs to my bedroom. After some bad directions from being upside down, I slid gently from his shoulders and placed on my bed.

“Raise your hips,” he whispered.

I did as he asked and he expertly unzipped the back of my skirt, pulling it down to reveal my suspender belt with my stockings attached. My shirt had fallen away from my body since my skirt wasn't there to hold it in place and I was left lying on my bed in a white bra and thong. I heard his sharp intake of breath. I never intended to look sexy like this but thinking about it I guess it was quite a sight.

“You can’t be real. You look stunning,” he spoke as he placed his lips against my exposed belly, making my hips jerk in anticipation.

He started kissing my neck, nipping and licking as he descended down towards my wetness. He arrived at my breasts and marvelled at their size, not huge at a C cup, but my tiny waist made them look larger. He unclasped the front fastening and was greeted my erect pink nipples, standing to attention with the grace of his presence. He moaned lightly and placed his tongue on my sensitive nubs, sending electric shots to my pussy and making me moan in a low and sultry tone. 

Obviously a breast man, he gave my breasts some well needed attention, and decided to continue with his journey south. 

I felt his large but nimble fingers trace the elastic on my silk panties before hooking onto the corners to gently reveal my boss's object of desire. 

He gasped as my pussy was revealed to him, hairless and smooth. He smelt my aroma before he slowly glided his tongue on my opening.

"How can something so wrong feel this amazing?" I muttered through moans and gasps.

"It's obviously meant to be," he replied with his lips against me, sending vibrations through my electrified skin.

He continued his painfully slow pace, watching my body writhe and buck when he focused on my protruding bud. As I was intoxicated by the pleasure I was receiving, Sam decided to change speed and focus and his tongue expertly flicked all the right places. I felt my blood pressure rising, my vision blurred and I started to babble. I was in for one heck of an orgasm. He started to focus on my clit and that is when I lost control. I started to fall in orgasmic bliss, with wave after wave taking over my ability to control my body or mind.

"Saaaam, SAM! I'm... Oh god...” I couldn't even put a coherent sentence together; my mind and body were jelly and my boss was the culprit.

"I think it is safe to say you enjoyed that way more than you should have," Sam whispered.

"Hmmmm." That was my response.

"Well, I enjoyed it more than I should have." He started to kiss up my body, nipping along the way, and he met my lips with his. 

I gasped when I felt him poke my sensitive entrance with his manhood, being repetitive with the jabs. The eye contact we had was strong and there was no way of breaking the spell. Then he penetrated me with a brisk flick of the hips to the hilt. 

My boss and I were one at that moment, and I fucking loved it.

"Keep going Sam, I want this," I whispered.

His lips curled into a smile before he lowered his them to mine, kissing me fiendishly while gradually pumping harder and harder into me. The speed he managed was astonishing, and the moaning that exited my mouth was purely incoherent babble. He placed his finger on my clit and started flicking the pulsing bud in sync with his thrusts. My eyes began to cloud over and I was practically screaming.

"Sam, ssssaa... Oh god... Please... Harder... So much fucking harder... SAM!" I screamed as anther rush took over my body, my pussy milking his cock for his seed. His eyes began to roll back as he pumped harder, making the grasp my pussy had tighter, and he moaned too. 

I felt rope after rope of cum shoot deep inside me and it just prolonged my orgasm to the point that I blacked out, softly moaning while I fell into a deep slumber.


I woke the next morning with my face embedded in my pillow, not recalling the night before as reality. That was, until I smelt the divine aroma of bacon and coffee. I stretched, making the sheet around me fall and exposing my breasts. I suddenly remembered the previous night. 

I had royally screwed my chances at work; wouldn't it just be awkward now? I had to investigate so I threw on a nighty and silk dressing gown before making my way downstairs. 

"Morning!" Sam greeted really cheerfully. 

“Hey,” I responded, slightly confused.

I went to the fridge to collect some orange juice and I felt Sam's hands snake around my waist.

“Last night was amazing Nic,” he whispered.

Between kisses on my neck, I began to melt. “Sam, what are you wanting from this? ‘cos if all this was for a simple ‘wham bam, thank you ma’am’ I'm not sure I'd be able to work under you any more.”

He stifled a chuckle at my choice of words. “I have wanted you since I first laid eyes on you. I want us to be partners in more ways than one. Business and relationship, so no, this is not a fling.” 

I placed my arms around his neck and kissed him unashamedly on the lips.

“I could get used to that I guess.” I smirked.

“Well I guess your days of being cupid are over, you've got me to spend your spare time with now.” He beamed, hugging me close.

I snuggled into his neck. A perfect fit.

It was meant to be.

My boss, myself and I.